CH632731A5 - METHOD FOR PRODUCING ALKOXY-SUBSTITUTED POLYCYCLIC AROMATIC COMPOUNDS. - Google Patents

METHOD FOR PRODUCING ALKOXY-SUBSTITUTED POLYCYCLIC AROMATIC COMPOUNDS. Download PDF

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Publication number
CH632731A5
CH632731A5 CH27878A CH27878A CH632731A5 CH 632731 A5 CH632731 A5 CH 632731A5 CH 27878 A CH27878 A CH 27878A CH 27878 A CH27878 A CH 27878A CH 632731 A5 CH632731 A5 CH 632731A5
Authority
CH
Switzerland
Prior art keywords
formula
polycyclic aromatic
substituted polycyclic
aromatic compounds
reaction
Prior art date
Application number
CH27878A
Other languages
German (de)
Inventor
Maurice Dr Grelat
Claus D Dr Weis
Original Assignee
Ciba Geigy Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Priority to CH27878A priority Critical patent/CH632731A5/en
Priority to JP16131378A priority patent/JPS5497628A/en
Priority to JP16457078A priority patent/JPS54100368A/en
Priority to US06/001,573 priority patent/US4198529A/en
Priority to GB7900787A priority patent/GB2013658B/en
Priority to IT7947560A priority patent/IT7947560A0/en
Priority to DE2900630A priority patent/DE2900630C3/en
Priority to ES476710A priority patent/ES476710A1/en
Priority to FR7900571A priority patent/FR2414489A1/en
Priority to BR7900124A priority patent/BR7900124A/en
Priority to BE0/192833A priority patent/BE873405A/en
Publication of CH632731A5 publication Critical patent/CH632731A5/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C09B3/22—Dibenzanthrones; Isodibenzanthrones
    • C09B3/30—Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus
    • C09B3/36—Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus by etherification of hydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings

Description

Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von alkoxy-substituierten polycyclischen aromatischen Verbindungen. The present invention relates to a process for the preparation of alkoxy-substituted polycyclic aromatic compounds.

Aus der Literatur ist die Herstellung von alkoxy-substituierten polycyclischen Verbindungen durch Alkylie-rung der entsprechenden Hydroxyverbindungen mit üblichen Alkylierungsmitteln bekannt (vgl. Fiat Final Report Nr. 1313, Vol. II, Seiten 86 bis 87). The production of alkoxy-substituted polycyclic compounds by alkylation of the corresponding hydroxy compounds with conventional alkylating agents is known from the literature (cf. Fiat Final Report No. 1313, Vol. II, pages 86 to 87).

Die Alkylierung, besonders die Methylierung mit Sulfon-säureestern, ist teuer und muss in wasserfreiem Medium vorgenommen werden. Die Alkylierung mit Dialkylsulfaten, besonders Dimethylsulfat, weist der Eigenschaften der Verbindungen wegen einige Nachteile auf. The alkylation, especially the methylation with sulfonic acid esters, is expensive and must be carried out in an anhydrous medium. The alkylation with dialkyl sulfates, especially dimethyl sulfate, has some disadvantages due to the properties of the compounds.

Es wurde nun gefunden, dass man hydroxy-substituierte polycyclische aromatische Verbindungen in guten Ausbeuten mit Dialkylalkanphosphonaten unter Vermeidung der obengenannten Nachteile alkylieren kann. It has now been found that hydroxy-substituted polycyclic aromatic compounds can be alkylated in good yields with dialkylalkanephosphonates while avoiding the disadvantages mentioned above.

Das erfindungsgemässe Verfahren zur Herstellung von alkoxy-substituierten polycyclischen aromatischen Verbindungen der Formel The inventive method for the production of alkoxy-substituted polycyclic aromatic compounds of the formula

R10-R-0R1 R10-R-0R1

worin wherein

R einen unsubstituierten oder substituierten polycyclischen aromatischen Rest und R is an unsubstituted or substituted polycyclic aromatic radical and

Rj einen Alkylrest mit 1 bis 4, vorzugsweise 1 oder 2 Kohlenstoffatomen bedeuten, ist dadurch gekennzeichnet, dass man eine polycyclische Verbindung der Formel Rj is an alkyl radical having 1 to 4, preferably 1 or 2, carbon atoms, is characterized in that a polycyclic compound of the formula

HO-R-OH HO-R-OH

worin R die oben angegebene Bedeutung hat, mit einem Di-alkylalkanphosphonat der Formel wherein R has the meaning given above, with a di-alkylalkanephosphonate of the formula

O O

RI-^-(OR1)2 RI - ^ - (OR1) 2

worin Rj die oben angegebene Bedeutung hat, umsetzt. where Rj has the meaning given above.

Als polycyclische aromatische Reste R kommen z.B. der Naphthylen-, Anthrylen-, 2,7-Phenanthrylen-, 16,17-Violan-thrylen-, ein Isoviolanthrylen-, ein Pyranthrylen-, ein An-thanthrylen- oder ein m- oder p-Gligophenylenrest in Betracht. The polycyclic aromatic radicals R are e.g. the naphthylene, anthrylene, 2,7-phenanthrylene, 16,17-violan-thrylene, an isoviolanthrylene, a pyranthrylene, an an-thanthrylene or an m- or p-gligophenylene radical into consideration.

Als Substituenten der Reste R kommen hauptsächlich Halogenatome, vorzugsweise Chlor- oder Bromatome in Betracht. Substituents of the radicals R are mainly halogen atoms, preferably chlorine or bromine atoms.

Die Umsetzung kann in An- oder Abwesenheit einer Base und eines Lösungs- bzw. Verdünnungsmittels durchgeführt werden. The reaction can be carried out in the presence or absence of a base and a solvent or diluent.

Bevorzugte Basen sind Alkalimetallcarbonate und -bicarbonate, z.B. die des Natriums und des Kaliums, tertiäre Amine, wie z.B. Trialkylamine, vorzugsweise Triäthylamine oder Trialkanolamine, vorzugsweise Triäthanolamine oder Mischungen solcher Basen. Preferred bases are alkali metal carbonates and bicarbonates, e.g. those of sodium and potassium, tertiary amines such as e.g. Trialkylamines, preferably triethylamines or trialkanolamines, preferably triethanolamines or mixtures of such bases.

Als Lösungs- bzw. Verdünnungsmittel kommen übliche gegenüber den Reaktionsteilnehmern inerten Lösungsmittel wie z. B. Nitrobenzol oder Trichlorbenzol oder bei der Reaktionstemperatur flüssige Verbindungen wie Naphthalin in Betracht. Suitable solvents or diluents are customary solvents which are inert to the reactants, such as, for. As nitrobenzene or trichlorobenzene or liquid compounds such as naphthalene at the reaction temperature.

Die Reaktionstemperaturen betragen 130 bis 230 °C, vorzugsweise 150 bis 210 °C. The reaction temperatures are 130 to 230 ° C, preferably 150 to 210 ° C.

5 5

10 10th

15 15

20 20th

25 25th

30 30th

35 35

40 40

45 45

50 50

55 55

60 60

65 65

3 3rd

632731 632731

Von besonderem Interesse ist die Herstellung der Verbindung der Formel durch Umsetzung der Verbindung der Formel Of particular interest is the preparation of the compound of the formula by reacting the compound of the formula

HO OH HO OH

mit Dimethylmethanphosphonat der Formel with dimethyl methane phosphonate of the formula

O O

CH34-(OCH3)2 CH34- (OCH3) 2

Die erfindungsgemäss herstellbaren Verbindungen sind wertvolle Zwischenprodukte zur Herstellung von Farbstoffen oder stellen Farbstoffe oder Scintillatoren dar [vgl. GB Patentschrift 311 661 und Chemiker Zeitung 15, 517 ff (1965)]. The compounds which can be prepared according to the invention are valuable intermediates for the production of dyes or are dyes or scintillators [cf. GB patent specification 311 661 and Chemiker Zeitung 15, 517 ff (1965)].

Die nachfolgenden Beispiele veranschaulichen die Erfindung. Prozente sind Gewichtsprozente. The following examples illustrate the invention. Percentages are percentages by weight.

Beispiel 1 example 1

In 120 g Nitrobenzol werden 2,5 g Dimethylanilin und 30 g 16,17-Dihydroxyviolanthron der Formel 2.5 g of dimethylaniline and 30 g of 16,17-dihydroxyviolanthrone of the formula are in 120 g of nitrobenzene

(100) (100)

io 45 g Natriumcarbonat und 60 g Dimethylmethanphosphonat zugegeben. Die Reaktionsmischung wird innerhalb 2 Stunden unter Rühren auf 200 °C erhitzt und bei dieser Temperatur 4 Stunden lang reagieren gelassen, wobei etwas Wasser abdestilliert. Die Reaktionsmischung wird auf 80-100 °C i5 abgekühlt, und der entstandene Niederschlag wird abgesaugt. Der Rückstand wird mit Wasserdampf destilliert, und man erhält in guter Ausbeute den grünen Küpenfarbstoff der Formel 45 g of sodium carbonate and 60 g of dimethyl methanephosphonate were added. The reaction mixture is heated to 200 ° C. in the course of 2 hours with stirring and left to react at this temperature for 4 hours, some water being distilled off. The reaction mixture is cooled to 80-100 ° C. 15 and the precipitate formed is suction filtered. The residue is distilled with steam and the green vat dye of the formula is obtained in good yield

(101) (101)

25 25th

als bronzefarbige Kristalle. as bronze colored crystals.

30 Beispiel 2 30 Example 2

19 Teile 16,17-Dihydroxyviolanthron, 50 Teile Natriumcarbonat, 2 Teile N,N-Dimethylanilin und 120 Teile Dimethylmethanphosphonat werden unter Rühren bis auf 50 °C erwärmt und 1 Stunde bei dieser Temperatur gerührt. Die 35 Temperatur des Reaktionsgemisches wird auf 130 °C und nach 30 Minuten auf 170-175 °C erhöht. Bei dieser Temperatur lässt man 6 Stunden rühren. Das gebildete Wasser wird durch Destillation entfernt. Bei 90-100 °C wird der gebildete Farbstoff abfiltriert und mit warmem Dimethyl-40 methanphosphonat gewaschen. Der rohe Presskuchen wird mit Wasser gekocht, abgesaugt, neutral gewaschen und getrocknet. Man erhält in guter Ausbeute das bronzefarbige kristalline Produkt der Formel (101), welches Baumwolle aus blauer Küpe grün färbt. 19 parts of 16,17-dihydroxyviolanthrone, 50 parts of sodium carbonate, 2 parts of N, N-dimethylaniline and 120 parts of dimethyl methanephosphonate are heated to 50 ° C. with stirring and stirred at this temperature for 1 hour. The temperature of the reaction mixture is raised to 130 ° C and after 30 minutes to 170-175 ° C. At this temperature, the mixture is left to stir for 6 hours. The water formed is removed by distillation. The dye formed is filtered off at 90-100 ° C. and washed with warm dimethyl 40 methanephosphonate. The raw press cake is boiled with water, suction filtered, washed neutral and dried. The bronze-colored crystalline product of the formula (101), which dyes cotton from blue vats green, is obtained in good yield.

Claims (5)

632 731632 731 1. Verfahren zur Herstellung von alkoxy-substituierten polycyclischen aromatischen Verbindungen der Formel 1. Process for the preparation of alkoxy-substituted polycyclic aromatic compounds of the formula RjO-R-ORi worin RjO-R-ORi wherein R einen unsubstituierten oder substituierten polycyclischen aromatischen Rest und R is an unsubstituted or substituted polycyclic aromatic radical and Rj einen Alkylrest mit 1 bis 4 Kohlenstoffatomen bedeuten, dadurch gekennzeichnet, dass man eine poly-cyclische aromatische Verbindung der Formel Rj is an alkyl radical having 1 to 4 carbon atoms, characterized in that a polycyclic aromatic compound of the formula HO-R-OH HO-R-OH worin wherein R die oben angegebene Bedeutung hat, mit einem Dial-kylalkanphosphonat der Formel R has the meaning given above, with a dialkylalkanephosphonate of the formula 9 9 Ri~P-(ORI)2 Ri ~ P- (ORI) 2 worin wherein Ri die oben angegebene Bedeutung hat, umsetzt. Ri has the meaning given above. 2. Verfahren gemäss Anspruch 1 zur Herstellung der Verbindung der Formel 2. The method according to claim 1 for the preparation of the compound of formula OCH OCH durch Umsetzung der Verbindung der Formel by reacting the compound of the formula HO OH HO OH mit Dimethylmethanphosphonat der Formel with dimethyl methane phosphonate of the formula O O CH34-(OCH3)2 CH34- (OCH3) 2 2 2nd PATENTANSPRÜCHE PATENT CLAIMS 3. Verfahren gemäss Anspruch 1, dadurch gekennzeichnet, dass die Umsetzung in An- oder Abwesenheit einer Base durchgeführt wird. 3. The method according to claim 1, characterized in that the reaction is carried out in the presence or absence of a base. 4. Verfahren gemäss Anspruch 1, dadurch gekennzeichnet, dass die Umsetzung in An- oder Abwesenheit eines Lö-sungs- bzw. Verdünnungsmittels durchgeführt wird. 4. The method according to claim 1, characterized in that the reaction is carried out in the presence or absence of a solvent or diluent. 5. Verfahren gemäss Anspruch 1, dadurch gekennzeichnet, dass die Umsetzung bei Temperaturen zwischen 130 und 230 °C durchgeführt wird. 5. The method according to claim 1, characterized in that the reaction is carried out at temperatures between 130 and 230 ° C.
CH27878A 1978-01-11 1978-01-11 METHOD FOR PRODUCING ALKOXY-SUBSTITUTED POLYCYCLIC AROMATIC COMPOUNDS. CH632731A5 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
CH27878A CH632731A5 (en) 1978-01-11 1978-01-11 METHOD FOR PRODUCING ALKOXY-SUBSTITUTED POLYCYCLIC AROMATIC COMPOUNDS.
JP16131378A JPS5497628A (en) 1978-01-11 1978-12-28 Preparation of alcoxy substituted polycyclic aromatic compounds
JP16457078A JPS54100368A (en) 1978-01-11 1978-12-30 Phenoxyalkyl oxazoline*its manufacture and herbicide containing it
US06/001,573 US4198529A (en) 1978-01-11 1979-01-08 Process for the production of alkoxy-substituted polycyclic aromatic compounds
GB7900787A GB2013658B (en) 1978-01-11 1979-01-09 Process for the production of alkoxy substituted polycyclic aromatic compounds
IT7947560A IT7947560A0 (en) 1978-01-11 1979-01-09 PROCEDURE FOR THE PRODUCTION OF ALKOXY-SUBSTITUTED POLYCYCLIC AROMATIC COMPOUNDS
DE2900630A DE2900630C3 (en) 1978-01-11 1979-01-09 Process for the preparation of alkoxy-substituted aromatic compounds
ES476710A ES476710A1 (en) 1978-01-11 1979-01-10 Process for the production of alkoxy-substituted polycyclic aromatic compounds
FR7900571A FR2414489A1 (en) 1978-01-11 1979-01-10 PROCESS FOR THE PREPARATION OF AROMATIC, POLYCYCLIC COMPOUNDS SUBSTITUTED BY ALCOXY GROUPS
BR7900124A BR7900124A (en) 1978-01-11 1979-01-10 PROCESS FOR THE PREPARATION OF POLYCYCLIC, AROMATIC COMPOUNDS REPLACED BY ALCOXI
BE0/192833A BE873405A (en) 1978-01-11 1979-01-11 PROCESS FOR THE PREPARATION OF AROMATIC, POLYCYCLIC COMPOUNDS SUBSTITUTED BY ALCOXY GROUPS

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH27878A CH632731A5 (en) 1978-01-11 1978-01-11 METHOD FOR PRODUCING ALKOXY-SUBSTITUTED POLYCYCLIC AROMATIC COMPOUNDS.

Publications (1)

Publication Number Publication Date
CH632731A5 true CH632731A5 (en) 1982-10-29

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ID=4183343

Family Applications (1)

Application Number Title Priority Date Filing Date
CH27878A CH632731A5 (en) 1978-01-11 1978-01-11 METHOD FOR PRODUCING ALKOXY-SUBSTITUTED POLYCYCLIC AROMATIC COMPOUNDS.

Country Status (9)

Country Link
US (1) US4198529A (en)
JP (2) JPS5497628A (en)
BE (1) BE873405A (en)
BR (1) BR7900124A (en)
CH (1) CH632731A5 (en)
DE (1) DE2900630C3 (en)
ES (1) ES476710A1 (en)
FR (1) FR2414489A1 (en)
GB (1) GB2013658B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54141767A (en) * 1978-04-25 1979-11-05 Mitsui Toatsu Chem Inc Phenoxyphenoxyalkyloxazoline derivative and herbicides
US4414156A (en) * 1980-10-29 1983-11-08 Ciba-Geigy Ag Process for producing 2-methoxybenzanthrones
DE3133390A1 (en) * 1981-08-24 1983-03-10 Basf Ag, 6700 Ludwigshafen METHOD FOR AREA CONCENTRATION OF LIGHT AND NEW FLUORESCENT CONNECTIONS
DE3731809A1 (en) * 1987-09-22 1989-03-30 Basf Ag METHOD FOR PRODUCING ALKOXY (ISO) VIOLANTHREDIONS
DE58907554D1 (en) * 1988-08-05 1994-06-01 Basf Ag Phenoxyalkyl-substituted heteroaromatics, process for their preparation and their use for controlling pests.
US8129190B2 (en) * 2006-11-17 2012-03-06 Applied Nanotech Holdings, Inc. Tagged petroleum products and methods of detecting same
CN106243769B (en) * 2016-07-26 2017-08-25 安徽凯奇化工科技股份有限公司 A kind of preparation method of Vat Brilliant Green FFB

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE848982C (en) * 1946-03-26 1952-09-11 Ciba Geigy Process for the production of Kuepen dyes of the dialkoxydibenzanthrone and isodibenzanthrone series
US2935518A (en) * 1958-09-12 1960-05-03 Monsanto Chemicals Reaction products of tetrahalogenated quinoid compounds and trisecondary alkyl phosphites and process of making same
JPS52139034A (en) * 1976-05-13 1977-11-19 Ishihara Sangyo Kaisha Ltd Imide compounds and herbicidal composition containing the same
DE2861073D1 (en) * 1977-06-29 1981-12-03 Ciba Geigy Ag Pyridyloxy-phenoxy-alkanoic acid derivatives , processes for their preparation and their use as herbicides or plant growth regulators

Also Published As

Publication number Publication date
GB2013658A (en) 1979-08-15
DE2900630A1 (en) 1979-07-12
DE2900630C3 (en) 1981-07-16
FR2414489B1 (en) 1981-07-24
ES476710A1 (en) 1979-06-01
JPS5532738B2 (en) 1980-08-27
JPS5497628A (en) 1979-08-01
US4198529A (en) 1980-04-15
DE2900630B2 (en) 1980-08-21
JPS54100368A (en) 1979-08-08
FR2414489A1 (en) 1979-08-10
BE873405A (en) 1979-07-11
GB2013658B (en) 1982-06-03
BR7900124A (en) 1979-08-14

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